title: Enantioselective isomerization of primary allylic alcohols into chiral aldehydes with the tol-binap/dbapen/ruthenium(II) catalyst.
abstract: Efficient isomerization: The title reaction was catalyzed by the [RuCl2{(S)-tol-binap}{(R)-dbapen}]/KOH system in ethanol at 25 °C (see scheme). A series of E- and Z-configured aromatic and aliphatic allylic alcohols, including a simple primary alkyl-substituted compound (E)-3-methyl-2-hepten-1-ol, were transformed into the chiral aldehydes with at least 99 % ee. dbapen = 2-dibutylamino-1-phenylethylamine, tol-binap = 2,2'-bis(di-4-tolylphosphanyl)-1,1'-binaphthyl.
authors.affiliation: Division of Chemical Process Engineering and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.
authors.forename: Noriyoshi
authors.initials: N
authors.lastname: Arai
authors.forename: Keisuke
authors.initials: K
authors.lastname: Sato
authors.forename: Keita
authors.initials: K
authors.lastname: Azuma
authors.forename: Takeshi
authors.initials: T
authors.lastname: Ohkuma
keywords: aldehydes; allylic alcohols; asymmetric catalysis; isomerization; ruthenium